Transvestite Stories

1,024 results
Orientation
Length
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Infinite Scroll

Corporate Policy

by cmike on Sep 13, 2017
Transsexuals & Crossdressers

Paul was busy working on e-Mail when Tom stuck his head over the partition. "Paul - can I see you for a moment please?" As a director, Tom had a good reputation amongst the staff: fair, quiet, unassuming. He was one of the better leaders in the organisation, and he would often pick out staff to have chat with; so Paul felt comfortable standing up and follow...

The Door to Door Stocking Salesman Ch. 02

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Michele was thought about her first sexual encounter with the door to door stocking salesman; she had certainly enjoyed giving him a footjob and she would like to explore their burgeoning relationship further. She particularly liked it when he had kissed and cuddled her just before he left. Of course the dilemma was how to explain to him that she was a trans...

A Cissy & His Dildo

by pegboy on Oct 21, 2019
Toys & Masturbation

When I first moved in with Barbara, it was simply to split the living costs. She was a lesbian and wasn't interested in anything other than a casual friendship. But that didn't stop me from fantasizing about her. I did have one secret that I tried to keep from her. I love to wear women's clothing. I sometimes even fantasized about being a transvestite. But m...

Michele And The Predator Ch. 04

by MicheleNylons on Jul 15, 2020
Transgender & Crossdressers

Michele ended up sandwiched between the Predator and the stranger who occupied the corner of the booth. She heard her subjugator murmur something about 'red' which she didn't understand. She certainly understood the implication of the next sentence that he spoke, "Look what I bought us to play with!" Then she was forced to turn her face towards the Predato...

Maid to Order Ch. 04

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

While Michele slept Bill drove home very carefully aware that he was drunk and glad he didn't have far to drive. It took him three attempts to get his key in the front door lock but eventually he made it inside to find his wife snoring on the couch and the TV tuned to an all night shopping channel with the volume muted. Her skirt had ridden up exposing the d...

Transnational

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Malcolm Nyland was looking forward to his farewell party; he was leaving a job that had not only been a drudge, but had been a constant source of angst and worry. Malcolm worked for MI6; not in any capacity that involved glamour, mystique, danger or intrigue. Malcolm was a database analyst, and although he had a top secret security clearance, his job was on...

The Virgin Tranny & the Bride

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Basically, this is a true story of love told by my friend Robert and which I have changed only a little as it is already so sexy. All I had to do was suck her husbands dripping dick and then open her legs and lick out her cum-filled pussy. I was in state of turmoil. If I did it, I was accepting the next level in their pornographic world with a video and s...

Arabian Nights Pt. 04

by MicheleNylons on Sep 26, 2017
Transsexuals & Crossdressers

Back in her cell Sarina helps Michele undress. "That suit isn't too bad; you can just brush it and hang it up. That blouse will need a soak to get the come out of it. Check out your lingerie and stockings and if they have any rips or tears just ditch them. You get an allowance for lingerie and hosiery; the boys are always tearing them because they are so ro...

The Awakening Ch. 01

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Part One -- The Woman In The Mirror Dark; then light; my eyelids flutter. "Can he hear us?" a woman's voice. Dark; then light. "He's still comatose; but he's improving," an authoritative male voice. Light; now dark, the dream returns. I'm inside the mirror but I can't be seen. I try to reach through the glass but I can't. I try to speak but I am mute....

Lady In The House Ch. 10

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Michele decided to throw caution to the wind and to try to satisfy Davey to the best of her recently learned abilities. She dropped to her knees besides the bed and slowly eased down the zipper on Davey's fly. "What are you doing you naughty girl?" Davey joked. "I'm just reciprocating the pleasure you gave me," she smiled, and dipped her hand inside his je...